4-((4-Ethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)aniline → 2-(4-Imidazo[4,5-b]pyridin-3-yl-2-methyl-phenyl)-N-[4-(4-ethyl-piperazin-1-ylmethyl)-3-trifluoromethyl-phenyl]-acetamide

HRID 1661028Notes

Reaction equation

HRID 1661028 reaction equation
[N:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][C:17]([OH:19])=O)=[C:12]([CH3:20])[CH:11]=2)[CH:2]=1.[CH2:21]([N:23]1[CH2:28][CH2:27][N:26]([CH2:29][C:30]2[CH:35]=[CH:34][C:33]([NH2:36])=[CH:32][C:31]=2[C:37]([F:40])([F:39])[F:38])[CH2:25][CH2:24]1)[CH3:22]>C(Cl)Cl.CO>[N:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][C:17]([NH:36][C:33]3[CH:34]=[CH:35][C:30]([CH2:29][N:26]4[CH2:25][CH2:24][N:23]([CH2:21][CH3:22])[CH2:28][CH2:27]4)=[C:31]([C:37]([F:40])([F:39])[F:38])[CH:32]=3)=[O:19])=[C:12]([CH3:20])[CH:11]=2)[CH:2]=1

Participants

4

Reactant 2

HCID 591345644-((4-Ethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)anilineHCID 67021622(4-Imidazo[4,5-b]pyridin-3-yl-2-methyl-phenyl)-acetic acid

Product 1

HCID 670236352-(4-Imidazo[4,5-b]pyridin-3-yl-2-methyl-phenyl)-N-[4-(4-ethyl-piperazin-1-ylmethyl)-3-trifluoromethyl-phenyl]-acetamide

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The title compound is prepared as described in Example 7 but using (4-imidazo[4,5-b]pyridin-3-yl-2-methyl-phenyl)-acetic acid (Step 60.1) and 4-(4-ethyl-piperazin-1-ylmethyl)-3-trifluoromethyl-phenylamine (disclosed in WO 03/099771). Title compound: ES-MS: 537.0 [M+H]+; tR=3.18 min (System 1); Rf=0.16 (CH2Cl2/MeOH, 95:5+0.1% NH3aq).

Workup

  1. customThe title compound is prepared

Sources & evidence

ORD record
ord-6ab82e4f561a4047bacb6deaeb25479a
Source dataset
uspto-grants-2011_10
Patent number
US08030311B2

Reaction notes

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